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The purpose of this research study is two-fold: to assess the effectiveness of the school building and school district leadership programs within the School of Education at a large private university, and, to find areas for improvement. This study utilized a grounded theory research strategy using a case study of two campuses. Each case study utilized the same data collection methods and data analysis procedures in order to increase validity, reliability and generalizability. The key findings revealed that the graduates emphasized the importance of professional support via a cohort structure, a sound program philosophy, and a comprehensive and coherent curriculum. Thus, the findings suggest the program could be enhanced by the creation of leadership portfolios and quality administrative internships.